When You Don’t Want To Be The Boss Anymore with Chenell Tull


When You Don’t Want To Be The Boss Anymore with Chenell Tull

For those of you who follow me on Instagram, you know that recently I shared an Insta-story discussing the fact that lately I have not wanted to be the boss. It was difficult to share and difficult to feel, but I shared it because it’s bound to happen to every boss at some point. I knew it happened to Chenell Tull from a Facebook post she shared, so I asked Chenell, founder of hustletostartup.com, to join me today and talk about her story and how you can prevent boss-fatigue from ruining your boss career.

What are we drinking?

Chenell — Brooklyn Summer Ale

Shannon — Rosé

Podcast Notes

  • A month ago, Chenell wrote a blog post called When Your Business No Longer Makes You Happy
  • Chenell went to Arizona State and earned a geography degree. It was interesting, but there was no job path for her.
  • After college, Chenell got a job with AAA in their travel department. She sold hotel and car rentals for about six months. She then moved to their internet help desk and found her way into their marketing department.
  • While working, she started listening to Dave Ramsey’s, which turned her on to podcasts, and then found Pat Flynn’s of Smart Passive Income, and learned about marketing and showed her company how to do something with search engine optimization.
  • Friends and family asked her for marketing help with their businesses. She found herself working from 3:00 am and going to bed at 9:00 pm.
  • She quit her job a year ago and went out on her own. Chenell saw the opportunity to help smaller businesses. She could see the results and impact of her work. She also wanted to choose her schedule, instead of always working nine-to-five.
  • Chenell tried to talk herself out of going on her own. She saved up eight months of expenses and forced herself to quit her job.
  • For the first few months, she had a fun time choosing who she worked with and what she worked on. Her business has been growing and she doubled her income from working with AAA.
  • After the first several months, Chenell hit a wall with the work she was doing. She was hustling too hard and trying to get bigger and bigger projects to work on. She started to wake up dreading getting out of bed and she was drinking more than normal.
  • Shannon recently shared an Insta-story about this same feeling. She has been on the entrepreneurial roller coaster for almost five years. Over the last month or two, there was a series of things that were happening. Every issue felt like a lot and she didn’t want to be the boss anymore. Recently, she had a couple staff members leave for personal issues and she found herself being a little jealous that they could just tap out.
  • To get through this, Chenell decided to stop trying to get bigger clients and focus more on the clients she has now. She decided to start another side project to generate income, so when this happens again she will have a backup plan. She is also focusing on time-management and her mental health.
  • Both Chenell and Shannon have been meditating. Shannon uses the app Insight Timer. You can search different lengths and categories.
  • Shannon has a lot of friends who leave their jobs to be freelancers and they get burned out. When you go out on your own, it is easy to work seven days a week. Assessing your what you spend your time on is critical!
  • Don’t give up – figure out solutions. Figure out ways to deal with the pain. It is okay to acknowledge that sometimes it is not fun.
  • Matt Giovanisci did a podcast with Justin Jackson called Managing Mental Health While Working For Yourself
  • It isn’t usually a smack in the face, it usually is subtle. Shannon’s warning signs included not sleeping, drinking a lot, playing a game to numb her pain, and crying more.
  • There is a pressure to put on a happy face when you are a boss. It is lonely at the top, especially when there is a lot of stuff happening.
  • Sharing your story makes it more normal. Unhappiness happens when expectations are not met. When you start a business, sometimes it is going to suck. Go into it expecting that there will be down times.
  • Shannon talks about Oprah’s SuperSoul Conversations podcast.
  • Think of every breaking point as a test to see if you are going to keep pursuing your business. You won’t always love everything you are doing and that’s okay.
  • Build your business according to your goals and don’t quit!

TAKEAWAY: My biggest takeaway is to not let periods of challenge in your bossing career completely deter you from a path that you’re supposed to take. Find ways to manage stress or think through solutions that will help you stay happy and motivated while remaining the boss.

Random Three Questions 

  1. If you didn’t start this business, what else would you be doing?
  2. What is a show you like to binge watch?
  3. If you won a million dollars, what would you do with it?

Connect with Chenell

Website: hustletostartup.com


If you need someone to chat about your finances to see if it makes sense for you to become your own boss, I hope you’ll reach out to my team at the Financial Gym. One of the best roles my trainers play in their clients’ lives is being the sounding board you need for life’s tough money choices. You can schedule a free call here to find out more. No matter where you are in your financial journey, my financial trainers can help you get where you want to go. So head over to or send friends to financialgym.com/friends to sign up today!


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